Process for the preparation of pesticides

A process for the preparation of a compound of the formula

• and, where appropriate, their tautomers, in each case in the free form or salt form, in which
• either X is CH or N, Y is OR, and Z is O, or X is N, Y is NHR8 and Z is O, S or S(═O);
• R1 is C1-C4alkyl;
• R2 is H, C1-C4alkyl, halogeno-C1-C4alkyl, C3-C6cycloalkyl or C1-C4alkoxymethyl;
• R3 and R4 independently of one another are H, C1-C4alkyl, C1-C4alkoxy, OH, CN, NO2, a (C1-C4alkyl)3—Si group, where the alkyl groups can be identical or different, halogen, (C1-C4alkyl)S(═O)m, (halogeno-C1-C4alkyl)S(═O)m, halogeno-C1-C4alkyl or halogeno-C1-C4alkoxy;
• R5 is C1-C6alkyl, halogeno-C1-C6alkyl, C1-C6alkoxy, halogeno-C1-C6alkoxy, C1-C6alkylthio, halogen-C1-C6alkylthio, C1-C6alkylsulfinyl, halogeno-C1-C6alkylsulfinyl, C1-C6alkylsulfonyl, halogeno-C1-C6alkylsulfonyl, C1-C6alkoxy-C1-C6alkyl, halogeno-C1-C6alkoxy-C1-C6alkyl, C1-C6alkylthio-C1-C6alkyl, halogeno-C1-C6alkylthio-C1-C6alkyl, C1-C6alkylsulfinyl-C1-C6alkyl, halogeno-C1-C6-alkylsulfinyl-C1-C6alkyl, C1-C6-alkylsulfonyl-C1-C6alkyl, halogeno-C1-C6-alkylsulfonyl-C1-C6alkyl, C1-C6-alkylcarbonyl, halogeno-C1-C6-alkylcarbonyl, C1-C6-alkoxycarbonyl, halogeno-C1-C6-alkoxycarbonyl, C1-C6-alkylaminocarbonyl, C1-C6-alkoxyiminomethyl;
• di(C1-C6alkyl)-aminocarbonyl, where the alkyl groups can be identical or different;
• C1-C6-alkylaminothiocarbonyl;
• di(C1-C6alkyl)aminothiocarbonyl, where the alkyl groups can be identical or different;
• C1-C6-alkylamino, di(C1-C6alkyl)-amino, where the alkyl groups can be identical or different;
• halogen, NO2, CN, SF5, thioamido, thiocyanatomethyl;
• an unsubstituted or mono- to tetrasubstituted C1-C4alkylenedioxy group, where the substituents are selected from the group consisting of C1-C4alkyl and halogen;
• or QR6, where, if n is greater than 1, the radicals R5 can be identical or different;
• R6 is C2-C6alkenyl or C2-C6 alkynyl, which are unsubstituted or substituted by 1 to 3 halogen atoms;
• (C1-C4alkyl)3Si, where the alkyl groups can be identical or different;
• CN or an unsubstituted or mono- to pentasubstituted C3-C6cycloalkyl, aryl or heterocyclyl group, where the substituents are selected from the group consisting of halogen, C1-C6alkyl, halogeno-C1-C6alkyl, C1-C6alkoxy, halogeno-C1-C6alkoxy, phenoxy, naphthoxy and CN;
• A is a direct bond, C1-C10alkylene, —C(═O)—, —C(═S)— or halogeno-C1-C10alkylene and R7 is a radical R10, or A is C1-C10alkylene, —C(═O)—, —C(═S)— or halogeno-C1-C10alkylene and R7 is OR10, N(R10)2, where the radicals R10 can be identical or different, or —S(═O)qR10;
• R8 is H or C1-C4alkyl;
• R9 is methyl, fluoromethyl or difluoromethyl;
• R10 is H;
• an unsubstituted or substituted C1-C6alkyl, C2-C6alkenyl or C2-C6alkynyl group, where the substituents are selected from the group consisting of halogen;
• (C1-C4alkyl)3Si, where the alkyl groups can be identical or different;
• C3-C6cyclo-alkyl, which is unsubstituted or substituted by halogen;
• C1-C6alkoxycarbonyl, which is unsubstituted or substituted by halogen;
• unsubstituted or substituted aryl, where the substituents are selected from the group consisting of halogen, halogeno-C1-C4alkyl and CN;
• a (C1-C6alkyl)3Si group, where the alkyl groups can be identical or different;
• C3-C6cycloalkyl, which is unsubstituted or substituted by halogen;
• C1-C6alkoxycarbonyl which is unsubstituted or substituted by halogen;
• or an unsubstituted or substituted aryl or heterocyclyl group, where the substituents are selected from the group consisting of halogen and halogeno-C1-C4alkyl;
• Q is a direct bond, C1-C8alkylene, C2-C6alkenylene, C2-C6alkynylene, O, O(C1-C6alkylene), (C1-C6alkylene)O, S(═O)p, S(═O)p(C1-C6alkylene) or (C1-C6alkylene)S(═O)p;
• m is 0, 1 or 2;
• n is 0, 1, 2, 3, 4 or 5;
• p is 0, 1 or 2;
• and
• q is 0, 1 or 2,
• and the C═N double bond marked with E has the E configuration, which comprises
• a2) reacting a compound of the formula
• in which A, R2, R5, R7 and n are as defined for formula (I) and the C═N double bond marked with E has the E configuration, or a tautomer thereof, in each case in the free form or in the salt form, with a compound of the formula
• in which X, Y, Z, R3, R4 and R9 are as defined for formula (I), or, if appropriate, a tautomer thereof, in each case in the free form or in salt form, wherein the compound of formula (IV) is obtained by
• b1) reacting a compound of the formula
• in which R2, R5 and n are as defined for formula (I) and the C═N double bond marked with E has the E configuration, or a tautomer thereof, in each case in the free form or in salt form, with a compound of the formula
• R7—A—X2 (VII),
• in which A and R7 are as defined for formula (I) and X2 is a leaving group, wherein the compound of formula (VI) is obtained by
• c) reacting a compound of the formula
• in which R2, R5 and n are as defined for formula (I), or a tautomer thereof, in each case in the free form or in salt form, with a C1-C6alkyl nitrite.